EP0452755A1 - Procédé de préparation en continu de 1-halogène-1-oxophospholènes - Google Patents
Procédé de préparation en continu de 1-halogène-1-oxophospholènes Download PDFInfo
- Publication number
- EP0452755A1 EP0452755A1 EP91105457A EP91105457A EP0452755A1 EP 0452755 A1 EP0452755 A1 EP 0452755A1 EP 91105457 A EP91105457 A EP 91105457A EP 91105457 A EP91105457 A EP 91105457A EP 0452755 A1 EP0452755 A1 EP 0452755A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- bromine
- chlorine
- reaction
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000010924 continuous production Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 23
- 229910052794 bromium Inorganic materials 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 23
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 22
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- 229910052698 phosphorus Inorganic materials 0.000 claims description 15
- 239000011574 phosphorus Substances 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 5
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000011065 in-situ storage Methods 0.000 claims 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 13
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 12
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 8
- -1 bromine (C1-C4) alkyl radicals Chemical group 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 5
- HCSDJECSMANTCX-UHFFFAOYSA-N dichloro(methoxy)phosphane Chemical compound COP(Cl)Cl HCSDJECSMANTCX-UHFFFAOYSA-N 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- LRFHTGXVAPKMQG-UHFFFAOYSA-N 1-chloro-3-methyl-1lambda5-phosphole 1-oxide Chemical compound CC1=CP(Cl)(=O)C=C1 LRFHTGXVAPKMQG-UHFFFAOYSA-N 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
- CVWUIWZKLYGDNJ-UHFFFAOYSA-N tripentyl phosphite Chemical compound CCCCCOP(OCCCCC)OCCCCC CVWUIWZKLYGDNJ-UHFFFAOYSA-N 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- NGGOLKYHIKQDQB-UHFFFAOYSA-N 1-chloro-4-methyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical class CC1=CP(Cl)(=O)CC1 NGGOLKYHIKQDQB-UHFFFAOYSA-N 0.000 description 1
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical class N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- JCUUAFHQRWGIBU-UHFFFAOYSA-N ClP1(C=CC=C1)=O Chemical compound ClP1(C=CC=C1)=O JCUUAFHQRWGIBU-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- YGZSVWMBUCGDCV-UHFFFAOYSA-N chloro(methyl)silane Chemical class C[SiH2]Cl YGZSVWMBUCGDCV-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 1
- ILLOBGFGKYTZRO-UHFFFAOYSA-N tris(2-ethylhexyl) phosphite Chemical compound CCCCC(CC)COP(OCC(CC)CCCC)OCC(CC)CCCC ILLOBGFGKYTZRO-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65681—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a (thio)phosphinic acid or ester thereof
Definitions
- the invention relates to a process for the preparation of 1-halo-1-oxophospholenes by continuous reaction of alkoxydihalophosphines with 1,3-dienes.
- 1-Halogen-1-oxophospholenes of the general formula in which the radicals R2, R3, R4 and R5 independently of one another are hydrogen, chlorine, bromine or optionally substituted with chlorine or bromine (C1-C4) alkyl radicals and X is chlorine or bromine, are important starting compounds, for example for substances which as flame retardant compounds are used in halogen-free plastic systems, as carbodiimidization catalysts or as fungicides.
- DE-PS 1 191 204 describes the direct addition of phosphorus trihalides to 1,3-dienes to trihalophospholenes, which are then combined with oxygen-donating substances such as water, alcohols, ketones, orthocarbonyl compounds, etc. to form 1-halo-1 -oxophospholenes are implemented.
- oxygen-donating substances such as water, alcohols, ketones, orthocarbonyl compounds, etc.
- Another method is based on phosphorous acid monoester dichlorides, which are added to 1,3-dienes in an autoclave and then split into 1-halo-1-oxophospholenes and alkyl halides or alkylene dihalides [BA Arbusov AO Vizel, YY Samitov and YF Tarenko, Izv , Akad, Nauk. SSSR, Ser. Khim (1967) (3), 648; NA Razumova, LJ Zubtsova and AA Petrov, Zh. Obsh. Khim. 40 (12), 2554, (1969)].
- reaction times can be shortened within certain limits by adding phosphorus trihalides [NN Bliznyuk, ZN Kvasha and AF Kolomiets, Zh. Obshch. Khim. 37, 1811 (1967)], but this also does not yet achieve economically justifiable, short reaction times.
- the invention relates to a process for the preparation of 1-halo-1-oxophospholenes by reacting monoalkyl phosphate dihalides with 1,3-dienes, the reaction being carried out continuously in one stage under pressure at elevated temperature using phosphorus trihalides as the solvent.
- R2, R3, R4 and R5 independently of one another are hydrogen, (C1-C4) alkyl, preferably (C1-C2) alkyl, optionally substituted with chlorine and / or bromine, the rest R1 is a (C1-C10) - Alkyl radical, preferably (C1-C5) alkyl, optionally substituted with chlorine and / or bromine and X can be chlorine or bromine.
- the phosphorus trihalide is preferably used in an excess of 75 to 125%.
- the intermediate products are formed according to the following scheme: where X is chlorine or bromine, R1 is a (C1-C10) alkyl radical, preferably a (C1-C5) alkyl radical, optionally substituted with chlorine and / or bromine and R6, R7, R8, R9 independently of one another for hydrogen, Chlorine, bromine, (C1-C4) alkyl, preferably (C1-C2-alkyl, optionally substituted with chlorine and / or bromine, (C5-C7) cycloalkyl or phenyl.
- Phosphorus trichloride or phosphorus tribromide can be used as phosphorus trihalides for the process according to the invention.
- the alkoxy dihalophosphines to be used according to the invention are compounds of the general formula R1OPX2, in which the radical R1 is a (C1-C10) alkyl radical, preferably a (C1-C5) alkyl radical, optionally substituted with chlorine and / or bromine, and X can be chlorine or bromine.
- R1OPX2 the radical R1 is a (C1-C10) alkyl radical, preferably a (C1-C5) alkyl radical, optionally substituted with chlorine and / or bromine
- X can be chlorine or bromine.
- the trialkyl phosphites of the general formula to be used in the special embodiment of the process according to the invention P (OR1) 3, where R1 has the meaning given above, can be, for example: trimethyl phosphite, triethyl phosphite, tri-isopropyl phosphite, tributyl phosphite, tripentyl phosphite, tris (2-ethyl-hexyl) phosphite and tri-2-chloroethyl phosphite, the low-boiling methyl or ethyl derivatives preference is given.
- the technical usability of the alkyl halides obtained as by-products in the reaction with phosphorus trihalide is an important criterion for the selection of the trialkyl phosphites. If methoxydichlorophosphine, prepared from phosphorus trichloride and methanol or by equilibration of phosphorus trichloride with trimethylphosphite, is used, 1-chloro-1-oxophosphole is obtained as a by-product of chloromethane, which can be used, for example, in the Rochow synthesis of methylchlorosilanes.
- R6, R7, R8 and R9 independently of one another hydrogen, chlorine, bromine, (C1-C4) alkyl, preferably (C1-C2) alkyl, optionally substituted with chlorine and / or bromine, (C5-C7) cycloalkyl or Phenyl are out of the question.
- R6, R7, R8 and R9 independently of one another hydrogen, chlorine, bromine, (C1-C4) alkyl, preferably (C1-C2) alkyl, optionally substituted with chlorine and / or bromine, (C5-C7) cycloalkyl or Phenyl are out of the question.
- Ethylene oxide, propylene oxide and epichlorohydrin are preferred.
- 1,3-dienes with the general formula are suitable as 1,3-dienes in which R2, R3, R4 and R5 can independently be hydrogen, chlorine, bromine, (C1-C4) alkyl, preferably (C1-C2) alkyl, optionally substituted with chlorine and / or bromine.
- Particularly suitable 1,3-dienes are, for example, butadiene, isoprene, chloroprene and 1-methyl-butadiene. Butadiene and isoprene are particularly preferred.
- reaction mixtures can additionally be mixed with polymerization inhibitors, such as, for example, phenothiazine, hydroquinone, p-tert-butylpyrocatechol, etc., in amounts of up to 1% by weight [Houben-Weyl, Methods of Organic Chemistry, Volume 14/1, p 26 ff].
- polymerization inhibitors such as, for example, phenothiazine, hydroquinone, p-tert-butylpyrocatechol, etc.
- the process according to the invention is preferably carried out in a temperature range between 50 ° C. and 180 ° C., the range between 100 ° C. and 150 ° C. being particularly preferred.
- reaction times depend on the temperatures used. For the preferred temperature range, they are generally between 15 minutes and 2 hours, in particular between 30 minutes and 1 hour.
- the method according to the invention can be carried out, for example, in the following manner:
- the feed materials are metered into a coolable mixing vessel by means of metering pumps, which at the same time also serves as a template for a pressure-resistant metering pump with which the reaction mixture is conveyed into a heatable pressure loop.
- a valve attached to the end of the pressure loop maintains the required pressure inside the loop. This pressure corresponds to the vapor pressure of the volatile components at the relevant reaction temperature.
- the reaction products are also discharged via the above-mentioned valve.
- the reaction mixture relaxes with cooling when leaving the reaction coil via a pressure maintaining valve and is collected in a raw product container. Most of the chloromethane escapes, is condensed in a brine cooler and collected in another container, also cooled with brine. The hourly throughputs are used to determine the yield.
- the crude product is heated at 80 ° C. under normal pressure.
- the excess phosphorus trichloride is drawn off at 20 mbar up to a bottom temperature of 70 ° C.
- the phosphorus trichloride is condensed on a brine cooler.
- the pressure during continuous driving is 10 bar.
- the quantity of reaction mixture collected in one hour is used to determine the yield.
- the basis for the yield determination is the amount of reaction mixture obtained in one hour, which after working up by distillation gives 494 g (90.5%) of an isomer mixture which consists of 56% 1-chloro-1-oxophospholen-3 and 44% 1- Chloro-1-oxophospholen-2 exists.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4012489A DE4012489A1 (de) | 1990-04-19 | 1990-04-19 | Verfahren zur herstellung von 1-halogen-1-oxophospholenen |
| DE4012489 | 1990-04-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0452755A1 true EP0452755A1 (fr) | 1991-10-23 |
| EP0452755B1 EP0452755B1 (fr) | 1996-05-22 |
Family
ID=6404666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP91105457A Expired - Lifetime EP0452755B1 (fr) | 1990-04-19 | 1991-04-06 | Procédé de préparation en continu de 1-halogène-1-oxophospholènes |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0452755B1 (fr) |
| JP (1) | JPH04234894A (fr) |
| CA (1) | CA2040603A1 (fr) |
| DE (2) | DE4012489A1 (fr) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5099071A (en) * | 1989-11-09 | 1992-03-24 | Imperial Chemical Industries Plc | Anthanthrone derivatives |
| EP0794191A1 (fr) | 1996-03-04 | 1997-09-10 | Hoechst Aktiengesellschaft | Sels d'oxydes de 1-hydroxy-dihydrophospholes et d'oxydes de 1-hydroxy-phospholanes et leur utilisation comme agents ignifugeants |
| US6229044B1 (en) | 1997-03-04 | 2001-05-08 | Ticona Gmbh Deutschland Kg | Alkyl-1-alkoxyethylphosphinous acid aluminum salts |
| US6252108B1 (en) | 1997-08-07 | 2001-06-26 | Ticona Gmbh | Method for producing aluminium salts of cyclic phosphinic acid |
| US6270560B1 (en) | 1997-03-04 | 2001-08-07 | Ticona Gmbh | Flameproof polymer moulding material |
| US6303674B1 (en) | 1997-03-04 | 2001-10-16 | Ticona Gmbh | Aluminium salts of alkylhydroxymethylphosphinic acids |
| US6307097B1 (en) | 1997-05-20 | 2001-10-23 | Ticona Gmbh | Method for producing aluminum salts of cyclic phosphinic acids |
| US6344158B1 (en) | 1999-01-30 | 2002-02-05 | Clariant Gmbh | Flame retardant combinations for thermoplastic polymers II |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19737727A1 (de) | 1997-08-29 | 1999-07-08 | Clariant Gmbh | Synergistische Flammschutzmittel-Kombination für Kunststoffe |
| KR20180081736A (ko) | 2015-11-13 | 2018-07-17 | 아이씨엘-아이피 아메리카 아이엔씨. | 폴리우레탄 및 폴리이소시아누레이트 포움용 반응성 난연제 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1956187A1 (de) * | 1969-11-07 | 1971-05-13 | Vnii Fitopatologii | Als Fungizide anwendbare Organophosphorverbindungen und Verfahren zu deren Herstellung |
| DE2919754A1 (de) * | 1979-05-16 | 1980-11-27 | Hoechst Ag | Verfahren zur herstellung von 1-halogen-1-oxo- delta hoch 3 -phospholenen |
-
1990
- 1990-04-19 DE DE4012489A patent/DE4012489A1/de not_active Withdrawn
-
1991
- 1991-04-06 EP EP91105457A patent/EP0452755B1/fr not_active Expired - Lifetime
- 1991-04-06 DE DE59107830T patent/DE59107830D1/de not_active Expired - Fee Related
- 1991-04-15 JP JP3108351A patent/JPH04234894A/ja active Pending
- 1991-04-16 CA CA002040603A patent/CA2040603A1/fr not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1956187A1 (de) * | 1969-11-07 | 1971-05-13 | Vnii Fitopatologii | Als Fungizide anwendbare Organophosphorverbindungen und Verfahren zu deren Herstellung |
| DE2919754A1 (de) * | 1979-05-16 | 1980-11-27 | Hoechst Ag | Verfahren zur herstellung von 1-halogen-1-oxo- delta hoch 3 -phospholenen |
Non-Patent Citations (1)
| Title |
|---|
| CHEMICAL ABSTRACTS, Band 69, 1. Juli - 22. Juli 1968, Columbus, Ohio, USA; N.K. BLIZNYUK et al.: "1-Chloro-1oxophosphacyclo- pentanes and some synthesis based on them", Seiten 293-294, Zusammenfassung-Nr. 2 985y * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5099071A (en) * | 1989-11-09 | 1992-03-24 | Imperial Chemical Industries Plc | Anthanthrone derivatives |
| EP0794191A1 (fr) | 1996-03-04 | 1997-09-10 | Hoechst Aktiengesellschaft | Sels d'oxydes de 1-hydroxy-dihydrophospholes et d'oxydes de 1-hydroxy-phospholanes et leur utilisation comme agents ignifugeants |
| US6229044B1 (en) | 1997-03-04 | 2001-05-08 | Ticona Gmbh Deutschland Kg | Alkyl-1-alkoxyethylphosphinous acid aluminum salts |
| US6270560B1 (en) | 1997-03-04 | 2001-08-07 | Ticona Gmbh | Flameproof polymer moulding material |
| US6303674B1 (en) | 1997-03-04 | 2001-10-16 | Ticona Gmbh | Aluminium salts of alkylhydroxymethylphosphinic acids |
| US6307097B1 (en) | 1997-05-20 | 2001-10-23 | Ticona Gmbh | Method for producing aluminum salts of cyclic phosphinic acids |
| US6252108B1 (en) | 1997-08-07 | 2001-06-26 | Ticona Gmbh | Method for producing aluminium salts of cyclic phosphinic acid |
| US6344158B1 (en) | 1999-01-30 | 2002-02-05 | Clariant Gmbh | Flame retardant combinations for thermoplastic polymers II |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0452755B1 (fr) | 1996-05-22 |
| DE4012489A1 (de) | 1991-10-24 |
| CA2040603A1 (fr) | 1991-10-20 |
| JPH04234894A (ja) | 1992-08-24 |
| DE59107830D1 (de) | 1996-06-27 |
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